Hip-hop impresario Christopher C. Hawkins, aka "C-Note" (Patton), has made a fortune running his Killah Ink empire, but money can't buy him everything, especially not entry into South Carolina's super-exclusive  and ultrawhite  Carolina Pines Golf & Polo Club. When C-Note asks for an application, snooty club president Cummings (Jeffrey Jones) immediately thinks he's come about a job, then informs him that club membership is invitation only, and even if C-Note were to find a sponsor, there are 600 applicants ahead of him on the five-year waiting list. C-Note has much better luck with the real-estate agent (Todd Sherry, doing a shameful, limp-wristed gay caricature), who sells him the large chunk of property that borders the club and that, thanks to a lease that has just expired, now includes the 17th hole  the perfect location for Killah Ink's latest loud and lewd rap video. Faced with all those greasy-bootied babes bumping and grinding to Lil' Wayne on his links, Cummings, on the advice of his lawyer, sexy Shannon Williams (Tamala Jones), relents: Cummings is afraid that such outrageous behavior might discourage the USGA from choosing the Carolina Pines as the next host of the U.S. Open. But Cummings warns C-Note that his membership is strictly probationary, and should he or any member of his rowdy entourage (which includes Sherri Shepherd, Faizon Love and Chase Tatum) break even the tiniest rule, he's out. Cummings then hires a photographer to follow C-Note around the club and hopefully catch him behaving badly. But getting C-Note "dis-membered" won't be easy, as his mission at the club is highly personal: His late father, a caddy at Carolina Pines, once broke the club's course record, and C-Note is determined to see that this long-ignored achievement is finally recognized at the elitist club.

The religious discrimination against Rodney Dangerfield's character implicit in CADDYSHACK is now a more apparent, but still unspoken, racial prejudice: Although no one comes out and says it, there are simply no black people at the Carolina Pines Golf & Polo Club, and it's clear that the club administrators are anxious to keep a certain element from spoiling their all-white fun. And the film absolutely validates all those unstated prejudices. C-Note, himself a middle-class, Dartmouth-educated businessman who probably has a lot more in common with the club officials than his own friends, cynically uses the bad behavior of his entourage to, as he pointedly admits, "stick it to the man." The only character on hand to counter those stereotypes is lawyer Shannon (Shepherd's smart and savvy Lady G is quickly reduced to another caricature as soon as she gets back with her boyfriend, a temperamental ex-con who went to jail for violating a restraining order), but she's ridiculed for being too light-skinned and is read as an uppity careerist by C-Note's mother (Jenifer Lewis), a widow with solid middle-class values who wonders when her son will stop playing the gangsta fool. It's with sincere Mrs. C-Note that the filmmakers would like you to think the heart of the film lies, but that's not where the entertainment's at: The so-called "laughs" are in the sight of C-Note's gang tearing up the links in his pimped out, NOS-driven Humvee golf cart; Faizon Love ruining other golfer's swings by rudely farting on the green; and Cummings' 15-year-old son, Wilson (played by 31-year-old comedic blight Andy Milonakis), getting a lesson in how to properly slap a stripper's ass.